Acetic Acid → HCID 69332948, 화합물

HRID 350582노트

반응식

HRID 350582 반응식
[F:1][CH:2]1[CH:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5][NH:4][CH2:3]1.[C:14]([O:18][C:19]([N:21]([CH2:23][CH:24]=O)[CH3:22])=[O:20])([CH3:17])([CH3:16])[CH3:15].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>C1COCC1>[F:1][CH:2]1[CH:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5][N:4]([CH2:24][CH2:23][N:21]([C:19]([O:18][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:20])[CH3:22])[CH2:3]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 10725881tert-butyl N-methyl-N-(2-oxoethyl)carbamateHCID 23511873Ethyl 3-fluoro-4-piperidinylacetate

생성물 1

HCID 69332948HCID 69332948, 화합물수율 56%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethyl 3-fluoro-4-piperidinylacetate (230 mg, 1.22 mmol) and 2-(N-tert-butoxy carbonyl-N-methylamino)acetaldehyde (211 mg, 1.22 mmol) in THF (5 mL) was added NaBH(OAc)3 (386 mg, 1.82 mmol) and acetic acid (70.0 mL, 1.22 mmol) at room temperature After being stirred for 24 hr, the reaction mixture was quenched by the addition of sat. NaHCO3 solution and extracted with EtOAc. The extracts were washed with brine, dried over Na2CO3, and concentrated to dryness. Chromatography of the residue with CHCl3-MeOH (6:1, v/v) as eluent gave ethyl 3-fluoro-1-[2-(N-tert-butoxycarbonyl-N-methylamino)ethyl]-4-piperidinylacetate (236 mg, 56%) as a reddish oil. 1H-NMR (CDCl3) δ 1.25 (t, J=7.1 Hz, 3H), 1.45 (s, 9H), 1.53 1.79 (m, 2H), 1.90–2.09 (m, 2H), 2.15 (dd, J=16.4, 7.1 Hz, 1H), 2.45–2.58 (m, 2H), 2.87 (s, 3H), 2.90–2.99 (m, 2H), 3.20 (m, 1H), 3.24–3.45 (m, 2H), 4.14 (q, J=7.1 Hz, 2H), 4.61, 4.73 (each broad s, 1H); ESI-MS m/z 347.

후처리

  1. customthe reaction mixture was quenched by the addition of sat. NaHCO3 solution
  2. extractionextracted with EtOAc
  3. washThe extracts were washed with brine
  4. dry with materialdried over Na2CO3
  5. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-6de074db09c448e2af18ce4da757ab8d
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179819B2

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